"How To is billed as a comedy, but that misses the mark of what it truly is," says Justin Sayles of John Wilson's HBO docuseries. "Wilson, who began the series as a collection of Vimeo shorts before linking up with (Nathan) Fielder, says that he spent two years collecting the footage that would make it into the show. Those thousands of hours of video are trimmed into small vignettes—a style he says he became obsessed with during his first job out of college when he worked for a private investigator distilling recordings to their 'most incriminating moments.' At times, the clips on the show are played for laughs, like when a man strolls down the street with a Pomeranian draped on his head. At others, they’re morbid, like the police picking up a cardigan from a puddle of blood or paramedics dropping a corpse as they carry it out of a brownstone. But there’s a lyrical nature to the way Wilson deploys the footage as he narrates each episode. When he mentions how people often camouflage their true feelings, he shows a man hiding behind a shrub. As he talks about 'things beginning to accumulate,' the camera sticks on a woman covered in at least a half-dozen pigeons. These are real people behaving naturally in the shadows. It’s the American Beauty plastic bag scene for 30 minutes, except the bag is dog sh*t, skunks trapped in ATM booths, and Kyle MacLachlan futilely swiping his MetroCard for 14 full seconds. There are stark reminders of the Before Times throughout How To’s run, which was filmed almost entirely before COVID-19 hit America. That begins with the episode titles: 'How to Make Small Talk' harkens back to the days before social distancing and Zoom Thanksgivings; the idea that sparked 'How to Split the Check' seems frivolous now as restaurants shutter across the country. But there’s something visceral about watching Wilson interact with his surroundings. He stands in crowds, chats up strangers, and walks about his city freely. Wilson doesn’t show pre-pandemic New York as a maskless utopia—at one point, 'How to Cover Your Furniture' detours into a meta-commentary on class and power—but he does lovingly document it, warts and all. You live through his camera, sometimes wondering whether the world that made How to possible will ever exist again."
John Wilson on making the poignant COVID-era How To finale: "Yeah, the risotto episode had probably the most rigid timeline, because it was day by day at that point," he says. "A lot of us weren’t really taking the virus that seriously before the shutdown began. We were in all these crowded spaces, so I was able to expand a much more compact timeline. But I couldn’t jump around as much in there, because you would notice. You could not fake the different ways that people were behaving. That was the strength of the episode — that maybe for the first time (the show) is on a historical track. The other stuff, you feel like you’re in this nebulous pre-COVID universe."
Wilson says he got a lot of texts from exes after the pilot aired: "The morning after the pilot aired a lot of people that I used to date all texted me around the same time," he tells The Last Laugh podcast. "I think just because I speak about my previous relationships in that episode and it’s kind of a revealing episode. It was just like a flood all at once and it was nice to hear from everyone again. But the reaction has been really interesting. Because I would always self-release stuff on Vimeo and the reaction was always kind of predictable. There would be a few die-hard fans that would share it. And for the most part, it would just have a very unremarkable premiere on the internet. And I just wasn’t prepared for it to become a conversation among people that I don’t really know. Originally I would just screen them for my roommates and that was the only real audience reaction I would receive. And then over the years, I would show them at a festival or a small venue, but it's just been really shocking to see people respond positively to the work, because I was afraid that it was going to be too niche for a prestige TV audience. But it seems like people are really thirsty for something that feels real."
Wilson says the nuance of everything is so much more interesting: "When I watch Property Brothers or some sh*t like that, I just really want to know what these people are actually like. I crave that extra dimension in these people” he says. “The carpenter that’s working on a house in one of those shows, the people that don’t usually get the microphone, I want to know how they feel about these very niche topics.”